An Unexpected Romance
by Shooshkipoo
Summary: For JuliaAurelia, Dean is tired of Anna constantly hitting on him, so he and Sam attempt to direct her attention to someone else. Not that easy, it turns out. Warnings: Silly, some OOCness and some light Anna bashing
1. Chapter 1

Slightly AU, cuz Uriel is still alive. Not pure crack this time, but still pretty silly and some OOC-ness. And I make fun of Anna a lot.

For JuliaAurelia, who mentioned that Anna needs to keep her hands off Dean. Then this story was born.

Disclaimer: I don't own Supernatural.

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Dean sat on a stool in a deserted bar, a shot glass in his hand. He was waiting for Sam to return from doing his business so they could go back the motel and sleep. Their last hunt had taken until five am, explaining the empty bar. He yawned, letting his eyes slip shut.

"Hi Deeeeean," cooed a female voice, over to his left. Dean groaned inwardly; he didn't look to see who it was, his fears confirmed when two pale hands slipped in front of his eyes.

"Guess who?" Dean resisted the urge to roll his eyes,

"Hi Anna." She giggled and removed her hands,

"How'd you know it was me?" _Because I made the mistake of sleeping with you once and now you won't leave me alone!_

"Lucky guess." Replied Dean, forcing the smile to remain on his face. This became increasingly difficult when she climbed onto his lap.

"So I was thinking, we should hang out today. You haven't got any plans, have you?" Dean froze, as Anna's hand started stroking absent-mindedly up his arm.

"Uh, yeah actually. Sam and I have this hunt, and we have leads. And this person got killed a few days ago, and we should probably, uh, check it out." Sam chose that moment to enter the room.

"Sammy!" cried Dean, "Tell Anna all about that thing we're hunting." Sam looked blank for a second, and then caught the look on Dean's face and Anna perched on his lap.

"Oh yeah," said Sam, trying to sound convincing, "I was just doing some research on the guy that got killed and it's really weird. I think we should call Bobby and ask him about it." The room was silent. Both boys kept their pretenses up, hoping that Anna would buy it.

"Ok," she finally said, mournfully, "I'll see you later Dean,"

Dean slumped in his seat; Sam chuckled and sat down next to him.

"Sammy," said Dean exhaustedly "Never become an actor."

"You should be thanking me," Sam retorted, "Next time I think I'll leave you at the mercy of the horny angel from hell."

"You wouldn't!" Dean sounded horrified. Sam grinned, he had blackmail material now!

"If you annoyed me enough, sure I would." Dean gulped.

"I just want her to go away! I know I'm irresistible, but this is getting ridiculous. Be thankful you aren't this attractive, Sammy."

Sam laughed again, picking up his beer.

"You know what you should do?" asked Sam, thoughtfully

"What?" Dean grunted

"Well, Anna is obsessing over you because she hasn't go anything else to do,"

"Hey!"

"So all you need to do is find someone else for her to crush on." Sam finished. Both brothers sipped their drinks.

"Ok, what other guys do we know?"

Plan A: Bobby

Bobby scrubbed a hand over his beard, and headed over to the door, grumbling.

"Hi Bobby!" He was greeted with the sight of both Winchester boys standing on his doorway, wearing big toothy grins, and shifting their weight almost guiltily.

"Hi boys," he replied cautiously "what brings you here?"

"Oh, no reason," sang Sam

"Apart from that we just really wanted to see you!" added Dean. The grins got wider, bouncing on their heels.

"Christo," said Bobby. Nothing happened, so he let them in.

"So Bobby," said Dean casually, sitting down, "met any ladies lately?"

"No…"

"Would you like to?"

"Not really," Sam and Dean exchanged nervous looks. Bobby lost his patience,

"I don't scare easy, and you boys are creeping me out. What's going on?" The hairs on Dean's neck stood up as he felt that presence again.

"Um, Sam, I think I left something in the car. It's really heavy too, wanna help me carry it?"

"Sure thing Dean!" Bobby blinked, he didn't think he'd ever seen them move that fast. Then he heard an unfamiliar voice say,

"Hi, who are you?" Bobby turned around and saw a young woman with red hair standing in the room.

"Bobby Singer, and you?"

"My name's Anna. Have you seen Dean anywhere?"

"Anna the angel?" asked Bobby, dodging her question. There was something unnerving about her.

"The very same, Stud," she purred, stepping forward.

"So uh," Bobby gulped, she kept coming closer! "Why are you looking for Dean?" She paused and considered him for a moment, then smiled. Bobby thought it looked like a leer more than anything.

"Doesn't matter now, I'd much rather have a more rugged, mature guy." She batted her eyelashes. Bobby shuddered.

Sam and Dean crouched behind a battered van listening intently. So far, they hadn't heard anything. Then suddenly they heard Bobby emit a very un-manly squawk preceding a gun shot. The brothers were frozen in fear, until they saw Bobby storm out of his house holding his rifle, looking murderous

"You brought her here! I'm going to throttle you!"

The boys ran for their lives. Plan A: failed.

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A/N: Like it so far? Let me know?

Shooshkipoo


	2. Chapter 2

Even more AU, because I wanted to include Ash. Just pretend the Roadhouse didn't burn down and that Ash didn't die.

Disclaimer: I don't own Supernatural

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Sam and Dean peered out from behind the bushes, praying that Bobby wouldn't follow them this far into the forest.

"Dean?" the brothers looked. Castiel stood behind them, hands in the pockets of his trench coat and wearing a confused expression.

"What are you doing?"

"Hiding." answered Dean, pulling Castiel to the ground. Pushing apart some branches, Sam looked at the road; thankfully, Bobby had appeared to have given up. Sam slumped onto the forest floor.

"What are we hiding from?" asked the angel. A light bulb went off over Dean's head.

Plan B: Castiel

"Hey Cas?" Sam's eyes widened. _He wouldn't. _"Would you be interested in possibly, I dunno, going out with Anna?" Castiel tilted his head to the side.

"Go…out with?" he asked slowly, unsure of what that meant. Sam covered his eyes.

"Yeah," said Dean, "All you would have to do is take her to a couple of nice places, buy her a present or two and possibly, I dunno, kiss her." Dean stopped when he saw that Castiel's eyes were the size of dinner plates. Dean waved a hand, but Castiel didn't blink.

"Deeeeeeaaan!" Anna sang from far away "I'm gonna find you!" In a snap decision, the brothers grabbed Castiel's arms, threw him into the clearing and started running again.

"Caaaaaaas, have you seen Dean anywhere?" she asked, sidling up to Castiel and taking his hand.

"Do. Not. Call me. Cas." She beamed,

"But, it's such a cute name" He glared at her, then said in his most manly growly voice,

"I am NOT cute!" He began to back away from her, but he backed into a tree. In his panic, he noticed her lips coming towards him. So he did the only thing he could: duck out of the way so she ended up kissing the tree and then run like mad.

Sam looked out the window of the car just in time to see Castiel burst through the trees, a wild look of panic on his face.

"It's her! Run for it!" he cried, running past.

"Come back!" they heard Anna's voice echo from the trees, getting louder and louder which could only mean one horrible thing: she was getting closer.

"DRIVE!" bellowed Sam. Plan B: failed

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The boys pulled into the Roadhouse parking lot. They would be safe here, at least for a little while.

"Hey boys," smiled Ellen from behind the bar, "What brings you here?"

"We need to see Ash," said Dean. Sam stomped on his foot.

"He's out back, but make sure you knock first," warned Ellen.

"Thanks,"

Plan C: Ash

"Dean, what the hell are you thinking?" hissed Sam, standing outside Ash's door.

"I'm thinking that Ash is as equally nutty as Anna and would therefore get along with her." Before Sam could stop him, Dean banged on the door.

"Dr. Badass! We need to talk to you!" then he grabbed Sam's arm and pulled him into the bathroom.

Ash answered the door in his boxers. He peered around the hallway, his gaze landing on the red-haired girl now standing in the hallway.

"Did…you call me?" he asked, confusedly "I could have sworn it was a guy…"

"Baby, I can be whatever you want me to be." Ash slammed the door and locked it, but alas; physical boundaries mean nothing to angels. The brothers winced as hey heard Ash wail,

"No! Nooooooooo!" but they couldn't move from their spot, for fear that she would hear them. Finally, Ash's screams subsided, and they heard her emerge and begin walking towards the bathroom.

Sam and Dean both jumped when they heard her knock on the door.

"Is anyone in there?" Both brothers looked around in panic,

"Uhhh, yes," said Dean, lowering his voice, "take my advice and don't order the chili cheesedogs," Sam made a farting noise with his arm and Dean grunted, hoping it sounded convincing.

"Dean is that you?" _S***!_

"I do not know anyone by that name." said Dean as he and Sam scrambled out the window.

"It is you! Open the door!" Anna screamed. When they didn't reply, she kicked the door down. The empty room made her angry.

"You can't get away that easy, Dean."

Back at the car, Sam's cell went off.

"Hello?"

"Sam?" It was Ellen, "What the heck just happened? You go in there to talk to Ash and the next thing I know, he's crouched in the corner in fetal position and saying that he's been violated." The brothers sighed. Plan C: failed.


	3. Chapter 3

Disclaimer: I don't own Supernatural.

Thank you to everyone who reviewed, this story has been a blast to write!

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In an effort to ditch Anna, the boys checked in to the most elaborate, fancy and expensive hotel they could find. They collapsed down onto the feather mattresses, relishing in their softness and their blissful albeit temporary safety. Dean sighed in frustration when he couldn't remember the angel-proof sigils he had seen one. Sure would come in handy every now and then. The brothers slept in heavenly peace, but alas, such peace could not last long.

"Morning, Mud-monkeys." The brothers woke with a start. Uriel grinned at them.

"I hear you've been having some issues," Sam groaned and fell back on his pillow,

"You have no idea," Uriel's grin widened,

"I think I do actually," with that, he bellowed at the top of his lungs,

"ANNA! THEY'RE UP HERE!" Dean's mouth dropped open,

"I knew you were evil!" he cried, jabbing a finger at the angel.

Plan D: Uriel

"Get him!" screamed Sam, jumping on Uriel's back from behind. Dean joined the fray, and together they managed to subdue Uriel and tie him to a chair.

"Have fun!" sang Dean as he and Sam sailed out the door. Uriel glared at them; at least, he would have, if Sam hadn't thought to blindfold him as well.

Sam and Dean darted through the hallways. Dean squeaked in terror when he heard a horribly familiar sounding voice placidly humming in the elevator. Sam grabbed Dean's arm and pulled him to the wall. The elevator dinged open and Anna stepped out, smiling. She skipped down the hallway, taking a minute to admire the mannequin display; five humans each in a different pose. There were three women and two men; one man was wearing sunglasses and had his arm around a woman and the other man had a baseball hat pulled down over his face. The women were all posed like models. After a moment, Anna skipped on; she had to find Dean!

Dean lowered the sunglasses slightly, just in time to see Anna turning the corner. He sighed in relief and took his arm off the mannequin.

"Psst!" he hissed to Sam, "She's gone!" Sam pulled the baseball hat off his shaggy brown hair, panting. Careful not to make a sound that might alert her, they tiptoed away. They couldn't risk the elevator; for fear that she would hear it. So they began sneaking down the stairs.

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Anna burst through the door to the hotel room door that supposedly belonged to the Winchesters. She stamped her foot in frustration when Dean was nowhere in sight. She was about to leave, when she noticed a figure tied to a chair. This ignited her libido (never a good thing) and she stepped forward to investigate. She tugged the blindfold off the man's face.

"Uriel!" she exclaimed in shock, "What happened?" Uriel stuck out his lower lip and refused to answer; he was too embarrassed to admit that two mud-monkeys had managed to tie him to a chair. She knelt down so she was looking straight into his eyes,

"Upset? Don't worry, I can make you feel all better," she breathed, running a hand down his bald head and coming to rest on his cheek. Uriel struggled in his bonds, bed sheets weren't supposed to be this strong! But it was no use; Anna cupped Uriel's face with both hands and pulled him towards her.

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Sam and Dean jumped in fright when they heard an earth shattering roar,

"WINCHESTERS!" Abandoning all dignity, the brothers stampeded down the stairs, tripping over their feet, pushing other people out of the way. They ran out the doors, sprinting towards the Impala. Before they reached it, a lightning bolt struck the ground, just metres in front of them. The sky rumbled and the brothers leapt over the crater, jumped into their car and began to drive, just as another lightning bolt struck the ground.

"MUD-MONKEYS! PREPARE TO BE SMITED!!!!" Dean drove as fast as he could; trying to keep ahead of the lightning bolts that kept shooting down from the sky.

Just when they thought there was no way out, they reached a tunnel. When the sky boomed angrily, but no lightning came, they realized that Uriel couldn't reach them.

"Great," said Sam, "Now we just need to stay in this tunnel for the rest of our lives!"

Plan D: Failed. Epically.

Dean covered his eyes and groaned,

"Sammy," he whimpered, "I don't think Anna will ever stop chasing me." This thought made him want to curl up in fetal position and start rocking back and forth, just as Ash had. So he did.

"I don't think Uriel will ever stop trying to kill us." This thought was enough to make Sam curl up beside his brother and begin rocking back and forth.

"I have no idea if Anna will ever stop chasing you or not," Sam and Dean looked up to see Castiel, eyeing them with what could almost be considered compassion. Both brothers stuck out their bottom lips, eyes tearing up.

"But I know who does," Castiel reached out and touched both boys foreheads.

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Chuck Shirley woke with a start, when three men suddenly appeared in his house.

"Sam? Dean?" he asked, picking himself off the floor, "What are you doing here?"

"We need to know something about the future." said Dean. Chuck shook his head,

"I'm not supposed to tell you anything, that scary old man said he'd do things I'd regret if I did."

"Please," begged Sam, "It's not that big a deal, we just need to know about the angel Anna," Chuck blinked,

"I haven't," he was cut off by the door bursting open. Castiel had been sensible and vanished, but the Winchesters were stuck. Anna stormed through the door.

"Dean," she growled, her voice low, "have you been avoiding me?" Dean plastered a smile on his face,

"Avoid you? Why on earth would I do that?" He grinned even bigger, but began to sweat when she started coming closer,

"You were! And that makes me very," her face split into a smile, "very angry." Sam cowered behind his big brother. Dean closed his eyes and waited for the worst to happen. But it never did.

Dean cracked an eye open. Anna had stopped moving, her mouth hanging slightly open in awe, her eyes staring unblinkingly at Dean's feet. He looked; Chuck was peering out from behind Dean's legs and staring at Anna with a similar expression. Regaining his senses, grabbed Sam's arm and jumped out of the way. Chuck stood up, his eyes never leaving Anna's.

"Hi, I am the prophet Chuck," he stuttered out. Anna smiled,

"I'm Anna, the angel." The pair stoof for a couple of seconds before Chuck reached out and with a burst of background violin music, pulled Anna towards him and pressed his lips to hers. She returned the kiss with gusto, putting a hand on the back of Chuck's head and pulling him in.

Sam and Dean gaped.

"That was…"

"Unexpected," They stared for a couple more seconds. Then, figuring that this was just one of those times when one should not ask questions but get the hell out of there while they had the chance, the boys walked away, wondering to themselves where the music was coming from.

END

A/N: That's it! Hope you liked it Julia! OK be honest, how many of you saw this coming?

Shooshkipoo


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